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The Jungle Gym - April 2019

Friends– Thanks, once again, for all the thoughtful feedback on last month's issue. I liked learning
The Jungle Gym
The Jungle Gym - April 2019
By Nick deWilde • Issue #3 • View online
Thanks, once again, for all the thoughtful feedback on last month’s issue. I liked learning about your productivity regimens. If there’s anything you’ve implemented that’s been impactful, I’d love to hear about it.
If this is the first issue you’re seeing, it either means we just met in the past month (👋) or I forgot to include you previously (sorry 😔). To get a sense for what this is all about, you can check out previous editions here.
With that, let’s get on to the good stuff.

Career Transitions and the Ladder of Legitimacy
(8 minute read)
By their nature, career transitions tend to involve a lot of self-centered thinking. What do I want to do with my life? What will make me feel fulfilled? These are important questions, but, they only solve part of the problem. There’s always a stakeholder on the other side who must agree to take on the risk that comes with fulfilling the career transitioner’s goals. The vast majority of time that person is a hiring manager.
This post provides a framework to describe how hiring managers think about taking on the risk that comes with employing a career transitoner. To illustrate, let’s start with a story:
Michelle, has finally had it with her job. She’s ready to leave, and even knows what kind of job she wants next. Like many people, Michelle logs onto Indeed or AngelList to start searching for open positions. She lobs out a few applications and waits for the responses to roll in.
What factors determine whether her applications turn into phone screens, or, if those phone screens turn into on-sites, and ultimately a new job?
The deciding factor is how much hiring risk she’s asking employers to take on. This type of risk can be seen in several ways:
  • Financial – the company must pay to hire, relocate, train and compensate Michelle. If things don’t work out, there’s also the additional cost of severance and potential litigation.
  • Time – employees will need to spend time hiring and training her. If she performs poorly, the team’s performance will also get dragged down by the ensuing drama.
  • Social – If Michelle gets fired, those who vouched for her will see their credibility damaged. And, if she turns out to be really toxic, other employees may leave to avoid having to work with her.
While the whole company shares in this risk, it’s the hiring manager who bears the largest share of it. A manager’s performance is judged by the output of his team. For the reasons above a bad hire can drag down the performance of a whole team. Since a poorly performing team can limit the manager’s career growth within the company, hiring managers tend to be naturally risk averse when bringing on new people.
Since it’s hard to know if a new hire will work out, most hiring managers try to cover their asses by hiring candidates with obvious signals of legitimacy. In the case a hire doesn’t work out, the hiring manager say, “well, who’d have thought that someone who worked at Google would have been such a bad fit here?” In the vein of the oft-cited saying that “no one ever got fired for buying IBM,” no one ever got fired for hiring from Google.
There are several different attributes that contribute to hiring risk, including:
  • Functional risk– does the candidate have the ability to accomplish the objectives of this role?
  • Stage risk – does the candidate have experience operating in a work environment like this one?
  • Culture risk – will the candidate’s values, attitudes, and habits mix well with the other people on this team?
  • Customer risk – does the candidate have experience solving problems or creating solutions for our customer?
  • Problem risk – has the candidate created solutions to solve this type of problem before?
  • Solution risk – how comfortable is the candidate with the process of building and selling this type of solution?
The way most hiring managers see it, the least risky employee is one who’s done the exact same job before, in as similar of a context as possible (for those who’ve been following this newsletter, you’ll note that I don’t believe this is the best recipe for a great hire).
The amount of hiring risk a candidate is asking a manager to take on is roughly equivalent to the riskiness of a candidate’s career transition. In other words, the more things Michelle tries to change from one job to the next, the more transition risk she’s taking on.
What to do about it
To deal with this risk you basically have two levers at your disposal:
  1. Offer more
  2. Ask for less
Offering more means you’re either expanding the abilities you can share with your employer or the time you can devote to work. In my experience, most transitioners tend to understand the value of this lever. They believe that by spending enough time building skills, or demonstrating how much time they will dedicate to the job, employers will give them a shot. While I, of course, believe this is an essential part of accomplishing any career transition I think it’s lever #2 that gives transitoners a better chance at overcoming hiring risk.
The catch 22 of any career transition is that hiring managers want to see that you have experience doing the job, but to get that experience you need a job that offers experience. So how can you convince an employer to give you a shot?
Ask for less.
In practice, this means making a smaller ask from the gatekeeper that’s standing in the way of you getting the experience you want. Once you’ve had the experience, you can then ask for slightly more. I think of this as climbing the ladder of legitimacy.
To illustrate, let’s return to Michelle. She’s an architect with dreams of landing a product design role at Slack. In her current role she represents almost every type of risk to her future hiring manager at Slack. She has no experience with Slack’s customer, problem, or solution. Furthermore, her architecture firm is significantly smaller, has grown much slower, and probably has a very different culture. What Michelle does have going for her is a functional skillset that shares a lot of similarities with digital product design.
Assuming Michelle has the intellect and motivation to build the skills she needs, let’s look at how she might climb the ladder of legitimacy to assuage her future hiring manager’s fears.
Rung #1: Contribute to or observe a project for free
This allows Michelle to get her hands dirty with digital product design while mitigating the risk of her involvement by involving more experienced people and not asking for money. While it may seem like a small ask to contribute to a project for free, she’s asking both the other contributors and the client to entrust her with sensitive information and their time.
Rung #2: Lead or play a major role on a project for free
To get here she’ll need to demonstrate that she can make the rest of the team look good by delivering a quality work product in a timely manner. In selecting which projects to work on, she may want to consider projects at companies that are similar to Slack.
Rung #3: Get paid for project work
This will likely be the hardest step of Michelle’s ladder. A few common ways to overcome the challenge of this step:
  • Tell clients they only have to pay if they find the work valuable or offer a money-back guarantee
  • Ask for a low rate
  • Keep the project scope small
  • Bring other members on the team with more legitimacy
Rung #4: Find a short-term contract with a client
She’s now asking to not only to get paid, but for more serious responsibility in return for ongoing payment. Of course the contract is limited so the client doesn’t need to fear giving her severance, if things don’t work. If she’s having trouble getting traction at this step, she can always offer her time and abilities for a lower hourly rate. Again, this will be a great opportunity to look for a company with some similarities to Slack.
Rung #5: Get a full-time role in the right function
While this may seem like the top rung of the ladder, Michelle may still be a ways off from her ideal role at Slack. Often, in order to get a company comfortable with making a full-time offer, it’s necessary to take a chance on a small company that no one has heard of or a larger company that’s lost its luster. For those who are able, I think it’s much better in the long run to compromise on taking a lower salary in exchange for a manager or team with more promise.
Rung #6: Land the dream job
Assuming Michelle has kicked ass at her last company, and has gained some relevant experience to match what she wants to do with Slack, she’s now in a much better position to put her hiring manager’s mind at ease.
Keep in mind, that for companies that are really hot (let’s say Slack in 2016, or a company like Opendoor today) she may be looking at a few more rungs between #5 and #6, but the same principles still hold.
In summary, here’s how I view the steps to accomplishing a career transition:
  1. Figure out your goal
  2. Develop an understanding of how much risk you’re asking an employer to take on
  3. Fill in the necessary skill gaps to make a contribution
  4. Gain experience by contributing your abilities, and asking little in return
  5. Find ways to represent the contributions you’ve made to future gatekeepers
  6. Repeat steps 3-5 by contributing in increasingly more meaningful ways, accompanied by slightly larger asks
And, of course, if you, or someone you care about, is going through a transition, don’t hesitate to reach out.
Reading Recommendations
(17 minute read)
Founders and investors have lots of great role models who write about their craft. Unfortunately, despite the number of great operators in the Valley, too few share their secrets for how they operate large teams at fast growing companies. One of the best people to pay attention to on this topic has to be Founders Fund investor, Keith Rabois.
Rabois launched his career at PayPal where he oversaw several functions as an Executive VP, then went on to take executive roles at both Linkedin and Square, and co-founded the fast growing startup, Opendoor. With that said, if anyone knows how to operate as an executive it’s Keith.
Here are some of my favorite nuggets of advice from Delian’s article about Keith:
  • Managers are judged based on the output of their team, divided by the number of people they needed to achieve it. So, make sure that any hire either raises the average productivity of the team or is a multiplier that increases the output of everyone on the team.
  • Managing people according to their output incentivizes employees to tackle short-term conservative projects that they know succeed. They may miss the experiments that could lead to unexpected outsized wins.
  • Avoid having team-members over-optimize for a single metric by pairing indicators. For example, by paying sales people only on contract value, they may be incentivized to close customers who will churn. So pairing a revenue metric with a churn metric, can be a good way to align incentives.
If you like this, I’d suggest you check out the Delian’s other essays documenting his learnings from Keith:
(1 hr watch)
In the past two weeks I’ve gone down a total rabbit hole on Peter Zeihan’s vision of the future of geopolitics, which is at once both frightening and fascinating. Here’s the broad outline:
Since the end of WWII, America has used its navy to promote free trade amongst its allies, leading to unprecedented peace and prosperity. However, since the fall of the Berlin Wall, our commitment to ensuring the global order, has been slowly eroding.
America’s pullback will lead to a disastrous decline in standards of living for those countries that have become reliant on global free trade (spoiler: thats’ most of them).
The fate of these countries will, once again, become subject to their geographic features and demographic makeup, which for most are quite unfavorable.
The U.S. will largely avoid this decline due to it’s:
  • Lack of reliance on global trade
  • Energy independence (stemming from the shale boom)
  • Relatively young demography
  • Relative ability to assimilate immigrants (also helpful for demographics)
  • Geographic insulation from most other countries
  • High quality agricultural land
  • Military supremacy
He also lists a handful of other unlikely countries that will ascend in this new world order (hint: it’s not who you think).
I’m no expert on geopolitics. So, I can’t be sure how accurate his predictions are. But if your life has any connection to the world outside this country, you owe it to yourself to listen to this talk. If you want to continue down the rabbit-hole, he’s got two books and is coming out with a third later this year.
(14 minute read)
I hate to say it, but over the past few months I’ve been turning into more of a pessimist about technology, and its role in humanity’s future. That’s thanks in no small part to Jeremiah’s criminally underrated blog, We Are Not Saved.
This post contrasts the thesis of economist Tyler Cowen’s latest book, Stubborn Attachments with futurist Nick Bostrom’s paper, The Vulnerable World Hypothesis. For those who aren’t familiar with the book, Cowen essentially argues:
  1. Our top moral priority should be preserving and improving humanity’s long-term future
  2. The way to do that is to maximize the rate of sustainable economic growth
  3. We should respect human rights while doing so.
I naturally gravitate toward Cowen’s view. However, Bostrom’s Vulnerable World Hypothesis made me think again. He analogizes discovering new technologies to drawing balls from an urn.
Drawing a ball from the urn represents developing a new technology (using a very broad definition of the word). White balls represent technology which is unquestionably good. (Think the smallpox vaccine.) Off-white balls may have some unfortunate side effects, but on net they’re still very beneficial, and as the balls get more grey their benefits become more ambiguous and the harms increase. A pure black ball represents a technology which is so bad in one way or another that it would effectively mean the end of humanity. Draw a black ball and the game is over.
There are only a handful of ways humanity can avoid drawing a black ball:
  1. We stop drawing balls
  2. We keep drawing balls, but there are no black balls in the urn. There is no technology that will irrevocably end humanity
  3. Growth fixes everything, even the existence of a black ball
  4. We keep drawing balls, but we implement draconian measures to prevent black balls from truly “ending the game”
I agree with the author that the first seems nearly impossible. The second and third seem too risky, given the odds, that I wouldn’t be willing to bet the future of humanity on it. That leaves a strong argument in favor of #4.
Assuming our goal is still to perpetuate the survival of humanity, I’m starting to think that we will need to start shifting our values away from ones that lead to thriving and happiness to ones that lead to survival. Does this mean a surveillance state, like the one China is building will be necessary to get us through the turmoil to come? I don’t know, but I’m certainly more open to the idea than I was a few months ago.
As I mentioned, I’ve been really enjoying reading and listening to this author (he makes podcast episodes from each post he writes). To get a better understanding of his world view, I’d suggest starting with this post.
(3 mins)
Let’s end with something lighter. Shall we?
From my last newsletter, you may have caught on to my fascination with time, and how people choose to spend it. Given the growing popularity of distributed teams and remote working, I’ve been interested to see how the lives of these employees differ from traditional office-workers.
Here are some of the more interesting things I learned from the post:
  • As of 2016 about 27% of full-time workers did at least some work outside of the workplace. That’s up from 23%, in 2006.
  • Non-remote workers spend a median of 35 minutes traveling (versus remote workers who spend zero minutes). That means switching to a remote job should save you about 8.87 days, over the course of a year.
  • Remote workers tend to work less in terms of median number of hours (7 hrs. 47 mins. vs 8 hrs. 20 mins). However there are a lot more remote workers that work under 100 minutes, and over 700 minutes per day.
The author, has produced several other amazing data visualizations breaking down:
They’re all short posts with amazing visualizations (like the one below). Definitely worth checking out.
If you’re hiring, share some info about what role you’re looking to fill, and I’ll try to pass it along to the right people.
If you’re looking for your next thing tell me a bit about what kind of role you’re looking forand I’ll keep my eyes peeled for interesting opportunities.
If you want to grab coffee with someone in a similar role, let me know and I’ll try to match you up with a peer.
Lastly, a special thanks to my fiancée, Ash for her help with copyediting. Any coherent sentences can be attributed to her. As always, if you have any thoughts, I’d love to hear them.
Until next time,
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Nick deWilde

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